


Bill Williamson gets Fucking Pegged

by MALLR4TS



Category: Red Dead Redemption (Video Games)
Genre: Cunnilingus, Dildos, Dom/sub, Embarrassment, F/M, Humiliation, Masturbation, Mistress, Nipple Play, Obedience, Orgasm Delay/Denial, Pegging, Praise Kink, Strap-Ons, dom!reader, sub!Bill
Language: English
Status: Completed
Published: 2020-12-19
Updated: 2020-12-19
Packaged: 2021-03-10 20:01:06
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 3,921
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28162836
Author URL: https://archiveofourown.org/users/MALLR4TS/pseuds/MALLR4TS
Summary: The title says it all, Bill finally gets strapped (and damn, he loves it)
Relationships: Bill Williamson/Reader
Comments: 2
Kudos: 30





	1. Chapter 1

**Author's Note:**

> this request took me forever bc my brain kept going brrrrrr. no cap i wanna peg that big boy so much 
> 
> Tumblr and Twitter are @MALLR4TS

For the first time in an extremely long time, the camp is quiet; most folk are on a mission, the others have trailed into town, leaving a small handful of people to guard the site, which essentially meant get drunk and hope nobody wanders into camp.   
  
You were one of the members on the mission, a late evening heist, one that would probably take you all night as the gang were certain that the law would show up. You weren't expected to be back until tomorrow, maybe later, meaning your sweetheart, Bill, was left by himself for the first time in months. He's a clingy partner but you wouldn't have him any other way, always curled up to you at night, or has you on his lap whenever you sit at the campfire. At least you're never cold.  
  
But with you out of camp, that meant Bill had to sort himself out tonight in more ways than one. He'd been a 'good boy', following up your plead when you'd asked him not to get blind drunk tonight, and he hadn't touched a drop of liquor. He'd ate supper and went to bed, mostly because he didn't want to linger around camp and let his thoughts get to him, worrying about how the heist is going and how you're doing.   
  
Once Bill got into bed, he cuddled up under the blankets and had a waft of your natural scent drift up his nose, making his heart ache over how much he misses you. He laid awake for quite some time, tossing and turning, trying to sleep but nothing was helping. Bill quickly decided that he'd get himself off as that always tires him out, so he unbuttoned his shirt and kicked off his pants, stroking his thick cock and fantasizing about you.   
  
Bill thought about all the generic things like your usual mushy sex, or the way you'll tease him throughout the day; but his mind trailed off down a road of some thoughts that hadn't crossed his mind for a lengthy amount of time. He's always been a sub, a bottom, enjoying being told what to do and devoting himself entirely to a person, and you're fully aware of how he feels about men.   
  
As happy as he is with you, he misses wrapping his lips around another mans cock as they tell him exactly how they're going to fuck him. He misses being pinned down to the bed as another man slides his length deep into Bill, eventually filling him up after Bill tightens around him and milks his release. If only there was some way he could enjoy those sensations again with you...   
  
Bill grumbles as he sits upright, pulling over his bag of personal belongings; generic items like clothes, soap, snacks, Brown Jacks brush, etc. He rummages through to the very bottom of the bag, pulling out a bagged item. Bill unfastens the smaller bag and pulls out a dildo, a short but thick one, similar to his own length. He's not used his toy since before you two got together, and you were in a well-established relationship.   
  
" _I'm gonna be rusty,_ " Bill thinks to himself as he gets comfortable again in bed, wetting his fingers and sliding them into his hole.   
  
There's a slight burn and Bill lets out a hiss, stopping abruptly and reminding himself to just breathe and relax. Within time, Bill's working himself open, scissoring his fingers as his other hand slowly pumps his shaft. When Bill finally feels ready, he slips his fingers out, wiping his saliva off on his thigh and sitting upright. He rummages through his bag again and pulls out some hair pomade, using the product as lube as he slicks up his dildo.   
  
Bill lies back down on his back, propping his knees up and reaching between them. He slowly pushes the toy inside, letting out a whimper as he begins to feel full. The sound Bill makes when the tip of the dildo brushes against his prostate makes his own cock twitch, a noise that hasn't escaped his lips in god knows how long. Bill ignores the slight burn, hungry to satisfy his need, picking up the pace quickly as he fucks himself.  
  
He's thankful the camp is quiet but Bill still bites onto his own pillow after he rolls onto his side, making it easier for him to toy himself. He cries into it, his face flustered, eyes scrunched shut. Bill allows himself to fall apart, knowing the camp is silent enough to do so, reminding himself that he deserves to enjoy this quiet time to himself however he wants.  
  
"Shit," Bill grumbles into the pillow, slowing his thrust down so he can push the dildo as deep as it'll go. His cock twitches heavily as it hits his prostate, his balls beginning to swell as his orgasm nears. Bill picks up the pace again, practically crying into the pillow as he hits his own prostate with every thrust.   
  
He rolls onto his back, rubbing his spare hand over his hairy pecs, trailing his fingertips across each of his nipples, playing with one bud then moving across to the other. The thought of you has been on his mind this whole time, though his thoughts are fuzzy and confused. He's unsure how you'd ever be able to fuck him like this; maybe you could thrust the toy into him, or maybe you'll find a stud to fuck him whilst you praise him and order him to eat your pussy, Bill's happy with either, but he really wishes it was you ploughing down into him right now.   
  
But Bill has no idea how to address these things to you, nor if you'd be into them. What if you humiliated him and dumped him on the spot? No, you're far too kind to ever do that to him. You've always been so supportive and open to Bill, maybe you'd find a way to make it work?   
  
  
Bill decides to just pretend it's you, not worrying about the fact that you don't have a cock. He fucks himself harder at the thought, sobbing into the pillow as his precum continues to drip from his length, soaking the bedroll, but he'll have time tomorrow to wash it before you return.   
  
"Bill?" A sudden voice calls out.  
  
Bill know exactly who it is but doesn't have even a split second to sort himself out. You enter your shared tent, instantly meeting the sight of Bill propped up on his elbow, his face a vibrant red with wide eyes, and his other hand reaching behind himself, gripping tightly to the toy between his cheeks.   
  
You stand there with wide eyes, almost dropping your share of the loot in shock as you take in the image of your sweetheart fucking himself whilst you were gone. Bill finally unfreezes and pulls the blanket over his body as he begins splurting out explanations.  
  
"It ain't what it looks like!" he almost screams, quickly pulling the blanket over his face as well, as if he could just hide from the situation.   
  
"Wha- well then-" you stutter. "Bill, it's alright, I ain't mad," you tell him, placing your loot in the corner of the tent, followed by the saddlebag slung over your shoulder. You ensure the tent is fastened before making your way over to Bill, who's tossing and turning under the blanket as he attempts to clean himself up without you seeing.   
  
You climb onto the bedroll, pulling the blanket from Bills face but he quickly snatches it back and covers himself again. "Bill, it's fine!" you remind him.   
  
"It ain't fine, you wasn't meant to see that," Bill pouts as he sits upright and rummages through his bag, still with the blanket covering himself. You can tell he's trying to get dressed, struggling to pull his pants on from underneath the blanket as it keeps getting stuck in the waistline of his pants.   
  
"Bill, I mean it, sweetheart. It's fine, I promise," you say as you peel the blanket from him again. This time, Bill allows you to remove the blanket but he lies back down and rolls onto his side, facing away from you, not wanting you to see his embarrassed face.  
  
You plant a kiss on his shoulder, trying not to laugh to yourself as Bill is barely dressed, and you know how adorable he looks whenever he pouts. "Bill, my love, it's alright. I think it's quite attractive that you enjoy that kinda stuff," you remind him as you quickly pull off your clothes and curl into bed behind him, attempting to be the big spoon despite Bill being double the size of you.   
  
"I... I don't wanna talk about it..." Bill quietly tells you, allow you to wrap your arm around his waist.  
  
"Alright, we won't," you softly tell him, placing another kiss on his shoulder and letting your eyes fall shut.   
  
You know Bill isn't mad at you, he could never be, he's just dealing with shock and embarrassment but it'll wear off eventually. Bill places his hand over yours, entwining your fingers between his; a small but simple gesture to reassure you that he's not mad at you. You spoon him a little tighter, curling up around him and drift off to sleep, Bill following after once his mind is at ease.  
  



	2. Chapter 2

It's been a week now since you caught Bill red-handed and he's still practically avoiding you. He'll still kiss and cuddle you though there's definitely been a barrier there, and he told you he had a headache when you tried it on with him the other night. He spends most of his time to himself, staying on the outskirts of camp, sometimes going off for a ride just so he can get away from it all. Even the camp has noticed that he seems off, asking if Bill is okay, then double-checking with you after he tells them that he's fine.   
  
You had to drag Bill out of camp, literally, yanking him over to the horses and forcing him to mount Brown Jack. He'd followed you into town with the assumption that you were just going to enjoy a bath and some quiet time together, which you had done, though Bill still seemed off even as you played into all his favourite things. He's never been able to resist you when you're straddled over his lap in the bath, making out with him as you rub your hands over his toned muscles, telling him how handsome he is between kisses.  
  
He's currently sat on the edge of the bed looking like a sad, soggy dog. He barely dried himself off before getting into some fresh clothes, but at least he'd given his hair a good scrub with the towel.   
  
"You still upset?" you question as you straddle him again, placing a gentle kiss to his cheek.   
  
"I told you, I don't wanna talk about it," Bill reminds you for the hundredth time this week, though he's not snapped at you (and never will.)   
  
"We don't have to, but I've got something that might make you _feel_ better," you tell him, placing your hands on his jawline and lifting his head to look at you.  
  
"What is it?" he questions.   
  
"Hmm, I won't tell you, but I will show you," you say as you place a kiss to his nose. "You've gotta keep your eyes shut until I say though, okay?"   
  
"Alright," Bill replies suspiciously. You steal a quick kiss from him, grinning from ear to ear as you de-mount him.   
  
Bill shuts his eyes, listening out to the way you're scurrying around the room. "You got that look on your face, you know the one," Bill tells you.   
  
"I'm just excited, okay? I was gonna keep this until your birthday but I think you need it now instead," you explain.   
  
"...does this mean I ain't getting a present on my birthday?" Bill quietly asks under his breath, grumbling slightly.   
  
"I'll get you something small to open on the day," you sigh, shaking your head to yourself.   
  
  
Another minute passes and you're unsure if you're ready, but you look alright in the mirror, so you shrug and tell yourself you can always adjust it later. "Alright, you can look," you tell Bill, still fiddling with the straps. It feels... different to wear, artificial yet hot, you're excited to use it. You turn to finally look at Bill who looks like he's just seen a ghost.   
  
"Well?" you ask as you approach, letting out a soft laugh as the strap bounces when you walk.   
  
"What... you... where..." Bill begins to stutter. You know by now how Bill speaks, his brain attempting to push out too many questions at once, but it's pretty easy to figure out what he's trying to say.   
  
"I was browsing through an adult catalogue when I came across it, I figured you're into that kinda stuff... well, I assumed, but why not try it, hm?" you tell him as you approach, standing between his knees, Bill still sitting on the edge of the bed.  
  
Bill remains silent, his face bright red, the blush trailing up to his forehead and over the tips of his ears. He doesn't know where to look, his eyes constantly flicking between you, the room, and the strap on. "What's a matter?" you question as you cup his chin. "You ain't keen on me fucking you? Don't wanna be punished cause you've been runnin' away from me all week?"   
  
Bill mutters your name as he looks up at you, turning redder by the second. You know by now just how to set him off, exactly what to say to make his cock throb, and it seems to already be working as you notice his erection pressed against the thick denim of his pants.  
  
"I know what you like, Bill. I am your sweetheart after all," you remind him, placing a kiss to his forehead. Bill takes the opportunity to place his hands on your waist, holding you tenderly but clearly eager to pull you onto him, though you've not given him permission to do that yet. "Is this what you'd like, my love?" you question.  
  
"...Yes please," Bill accepts with a small nod after gulping.  
  
"Yes please, what?" you question, your tone slightly firm but still soft.  
  
"Yes please... Miss," he corrects himself.  
  
"Good boy."  
  
  
"Now drop to your knees and suck," you order him, standing a few paces back. Bill slowly stands, towering over you for a few short moments before he settles down on his knees. His eyes flick to yours again before trailing down and settling on the strap on; he looks uncertain, like he knows what to do yet expects to treat this any differently, but settles on following with what he already knows.   
  
Bill places one hand on the base of your cock, holding your length steady so he can wrap his mouth around the tip. He doesn't jerk your length, he just begins by slowly bobbing his head along it, picking up speed within time. Once his mouth is taking most of your length, he moves his hand from the base of your cock, slipping it between your legs so he can run a thick finger over your folds, taking you by surprise.   
  
You let out a soft yelp as a finger is pushed into you, curling just how you like it, brushing over your g-spot within seconds as Bill knows exactly where it is. You hum in approval, parting your legs more to make Bills job easier. Another finger joins the one already inside of you, pumping in time with his mouth as he continues to suck on your cock.   
  
An idea comes to mind and you order Bill to stop. He does so instantly, looking up at you patiently for your next command. "Get those pants off and start prepping yourself, then stick your tongue out when you're ready," you instruct.  
  
"Yes, Miss," Bill replies with a nod.   
  
Bill makes quick work of his clothing, removing his pants and briefs and unbuttoning his shirt, letting his thick cock hit the cold air and hang untouched between his legs, the tip flushed as red as his cheeks were minutes ago. He sits on his knees again, reaching one hand between his legs after slipping two fingers into his mouth to slick them up. Bill lets out a soft grunt as he pushes them in, followed by a deep sigh.   
  
He finally looks up at you, swallowing nervously then sticking his tongue out and awaiting your next command. "Always so good for me, aren't you?" you praise as you run your fingers through his hair, locking your fist onto the back of his head. Bill nods in agreement, keeping his mouth open.   
  
You reposition yourself, parting your legs more as your other hand holds onto your cock, pulling it up and out of the way. You push your pussy down onto Bills tongue, rutting yourself over the muscle, getting yourself off on Bills face. He shuts his eyes, tilting his head back so you can slide over his tongue better. The stance is a little weird and uncomfortable, but you catch yourself in the mirror, practically standing over Bills face, running your hips however fast you want against him whilst he continues to prep himself. If only you could capture the sight.   
  
"Atta boy, keep that tongue out," you order him. You continue to get yourself off on his face, your body trembling more and more the closer you get to your orgasm. Your knees are beginning to ache, but thankfully you cum in time, panting and sighing heavily as you cum on Bills face. He hums again, resting his other hand on your thigh to keep you steady.   
  
You slip off Bills face, "c'mon, Bill. Get on the bed," you order him.   
  
"Yes, Miss," Bill replies, slipping his fingers from himself.  
  
  
Bill scrambles to his feet and gets comfortably on the bed, shuffling back against the covers, propping himself up on his elbows whilst he waits for you to join him. He's quite the sight with only his shirt on, hanging open to display his thick, broad, hairy chest. His cock hangs against his stomach, his balls already looking heavy and eager for release. Despite Bill being such a large guy that could easily overpower you at any second, he waits patiently as always, following your every order, never disobeying and feeding off all the praise you give him.  
  
You climb onto the bed, positioning yourself between his thighs. He begins to look embarrassed again, slightly awkward from the new experience; he's had you between his legs before but not like this. You coo him as one hand grips onto his thick thigh, pulling it against your waist as you position yourself. Your other hand holds the base of your cock, lining it up with Bills entrance and slowly pushing in. Your eyes flick up to meet Bills as the tip slips in, checking for any signs of discomfort; instead, that embarrassed look he had moments ago has slipped off and been replaced with lust.   
  
The more you push your cock in, the more Bill seems to relax, eventually letting out a soft grunt when you sheath yourself all the way in. "Good boy," you sigh, checking again to see if Bill is showing any signs of discomfort but he's not. You slowly pull most of your cock out, only to push into him again, a little faster this time. You repeat the process over and over, eventually slipping into a smooth yet slow rhythm.   
  
Bills head rolls back against the covers, his eyes falling shut as he lets out a deep sigh. His cheeks are bright red, almost as red as when he first saw you wearing the strap on. His eyes suddenly open to meet yours and you can tell he has something on the tip of his tongue.  
  
"You alright, sweetheart?" you question.   
  
"Mhmm," Bill says with a nod, biting at his bottom lip as his body shudders.   
  
"What's a matter?" you ask him again.   
  
"...Would you go faster please, Miss?" Bill politely asks.  
  
You nod in agreement and speed up your thrusts, fucking Bill both faster and harder. A moan finally slips from his lips, followed by another shudder moments later as you brush against his prostate. You pause for a moment, angling your hips and slamming into him, hitting his prostate yet again.   
  
"Shit!" Bill grumbles. He moves one hand down to touch his cock but quickly moves away, remembering that you haven't given him permission to do so yet.  
  
  
Now that you've found the right angle, you fuck him, fast and hard, the sound of skin against skin echoing around the hotel room. Bill begins to let out noises you haven't heard before, moans and whimpers, different to the ones he normally makes. He can barely keep his eyes open, his mouth remaining parted as you continue to peg the much larger man.   
  
"Is this what you wanted, Bill?" you flirtatiously ask, leaning forward so you can move a hand off his thigh to rub over his chest.   
  
"Y-yes, Miss," Bill stutters, nodding in agreement.   
  
He continues to whimper through gritted teeth, his cock turning redder by the second; he's clearly holding back on his orgasm, grabbing fistfuls of the blankets, his knuckles turning white as he continues to hold himself back. You've trained him well. You tweak at his nipples, noticing the way his cock twitches every time you do so. You flick from one to the other, taking your time to trail the palm of your hand across his pecs, admiring the thick fur that keeps him warm.  
  
Your hand soon moves from his chest to gently massage his balls, feeling how heavy and swollen they are. You hum in approval, your eyes flicking up, catching onto his as he continues to mewl against the covers.   
  
"Your balls feel so heavy, Bill. Do you want to cum?" you question.   
  
"Please... Miss," Bill sighs and nods.   
  
"You can cum once you've told me who's a good boy," you flirt, moving your hand from his balls to wrap around his length, slowly jerking him but your grip isn't tight enough to fetch his release.  
  
"I-I am," Bill gulps. "I'm a good boy," he informs you.   
  
"Course you are, you're my good boy," you say with a smile, tightening your grip around his cock. "Cum for me, Bill," you order him, quickly finding the right rhythm with your thrusts and jerks.  
  
  
Bill cums harder than he ever has before, his muscles vibrating as he coats his stomach and chest with his release. You slow your thrusts, eventually coming to a halt, watching as Bill pants heavily, his eyes shut and his arms sprawled out on the bed. He looks debauched, exhausted, ready to sleep for a week solid.   
  
You slip out of him, getting up and cleaning yourself off, followed by Bill. You get ready for bed after removing the strap, turning off the lanterns then urging Bill to get into bed. He had almost fallen asleep in the short time it'd taken you to clean both of you up, but grumbles slightly as he peels off his shirt and snuggles down into bed, cuddling up to you, resting his head on your chest and his arm loosely around your waist.   
  
Maybe you'll have to surprise him like this again? 


End file.
